Taking into account the obvious....which is concern for our friends & passengers, there's no actual 'requirement' for a PFD (or PDF) where Max is sailing. (Although you'd probably want to check with Boating NSW)

The rule in Queensland (up the road) is if there's no need for Boat Registration there's no requirement for any Marine compliance issues. (safety gear)....or even Drink Yakking for that matter. Exactly the same rulz if you were out on a Boogie Board.

But...of course common sense should always be the deciding factor and encouragement to wear one.

That suggests he has to wear a PFD if he has the sail up.NSW Maritime is "self-funding" these days, which means they get to keep any fines they levy, so they have become quite predatory, though it's the stink boats they tend to pick on.

"While boats that do not require registration are not obliged to carry compulsory safety equipment, it is strongly recommended appropriate equipment is taken in the event of an emergency. Lack of preparation could lead to a breach of the general safety obligation. Carry enough safety equipment to be prepared for the unexpected."

Is followed by ......all boats under 4.8M must have everyone wearing PFD's when crossing a bar.

I think that one of the problems with all bureaucratic-based organisations is that they quote 'rules' to you. And often, even people who sincerely try to follow the rules, have no comeback at that moment.

Perhaps something that I should do is to make a tiny doc, with the relevant bits of the rules that apply (and the URL that states them), and laminate it, to carry on board. I could make that small enough to permanently carry it in my PFD pocket.

In Australia, Victoria you are supposed to carry your fishing license on your person at all times when fishing, if you are scuba diving for scallops, you are classed as fishing. Fisheries do not supply laminated licenses not even if you take out a 3 or 5 year license, just a bit of paper, 2 year ago I was asked by fisheries to produce my license so I pulled out a ziplock plastic bag with some white paper mush floating around in it and said here it is!!! That did not go down very well even though I was just trying to follow their rules with what they supply.

The AI is 4.88m long so it would be exempt also. It would be interesting to know just what class of boat the AI/TI is under the regs. Under the new regs an OC-1 is only required to carry a PFD on board, not actually be worn!